With the help of Kant’s Critique of Pure Reason this paper aims to investigate the very possibility of philosophical reflection. Starting from a reading of two Eugen Fink texts, a phenomenologically discovered question is posed and a critical response attempted. It will be shown how, by orienting itself upon the subjective feeling of reason’s demand for the unconditioned, critical thought is then able to restrict itself to a valid use of reason, thus securing its own possibility. The transcendental methodology employed by Kant and the concept of pure apperception will also be discussed as key components in the facilitation of philosophical reflection. The Kantian response offered here is largely centred around the concept of transcendental illusion as discussed in the ‘Transcendental Dialectic’ and by taking related concepts such as transcendental reflection into consideration it is subsequently shown that, despite being raised here phenomenologically, the question of philosophical reflection is very much of interest to critical thought.